Isobutylamine → N1-Isobutyl-L-alaninamide

Boc-L-alanine (5.0 g, 26.4 mmol), isobutylamine (2.9 mL, 29.1 mmol), diisopropylethylamine (11.5 mL, 66 mmol), and HOBt (3.6 g, 26.4 mmol) in anhydrous DMF (15 mL) is stirred 15 min. EDC is added, and the reaction is stirred at room temperature 16 h. The reaction is diluted in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The residue is redissolved in 4N hydrochloric acid in dioxane (30 mL) and stirred for 2 h. The solution is concentrated under reduced pressure, dissolved in chloroform and washed with 1 N NaOH (aq). The aqueous layer is extracted with chloroform, and the pooled organics are dried (sodium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 145.2 [M+H]+.

1. washwashed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
2. dry with materialdried (magnesium sulfate)
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. dissolutionThe residue is redissolved in 4N hydrochloric acid in dioxane (30 mL)
6. stirringstirred for 2 h
7. concentrationThe solution is concentrated under reduced pressure
8. dissolutiondissolved in chloroform
9. washwashed with 1 N NaOH (aq)
10. extractionThe aqueous layer is extracted with chloroform
11. dry with materialthe pooled organics are dried (sodium sulfate)
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure

ORD record

ord-bf64f79f7e5d4bb78d2ab5f21743b1a6

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07727997B2